S(β-Cyanoethyl)-Z-cysteinyl histidine methyl ester | 137197-01-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: S(β-Cyanoethyl)-Z-cysteinyl histidine methyl ester
• CAS: 137197-01-4
• 化学式: C₂₁H₂₅N₅O₅S
• 分子量: 459.526
• InChiKey: WHDGOSAEWKCSCJ-ROUUACIJSA-N

物化性质

• 沸点：
  806.4±65.0 °C(Predicted)
• 密度：
  1.315±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.55
• 重原子数：
  32.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  146.2
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  L-组氨酸盐酸盐 在 1,3-丙二硫醇 、 硫酸 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 64.5h， 生成 S(β-Cyanoethyl)-Z-cysteinyl histidine methyl ester
  参考文献：
  名称：

  Synthesis of “ zinc finger ” template

  摘要：

  The zinc finger template brings about protein-DNA recognition. The first synthesis of a metal template which incorporates the essential features of the zinc finger motif and represented by structure (1) has been achieved from the key tripeptide, bis-N-benzyloxycarbonyl cystinyl di-histidine methyl ester (2), using a novel thiol-disulfide exchange and subsequent complexation. The cobalt motif (5) has been similarly prepared. FAB mass spectrum, 1D nmr, COSY and NOESY spectra, difference NOe of (1) and the UV of (5) are in very good agreement with a ligand distribution profile around the central tetrahedral metal ion similar to that deduced for natural and synthetic zinc finger proteins.The potential of (1) or its appropriate variants in the understanding of diverse facets of DNA recognition is discussed.

  DOI：

  10.1016/s0040-4020(01)88195-3

文献信息

• Highly efficient propane-1,3-dithiol mediated thiol–disulphide interchange: a facile and clean methodology for S–S reduction in peptides
  作者：Subramania Ranganathan、Narayanaswamy Jayaraman

  DOI：10.1039/c39910000934

  日期：——

  Propane-1,3-dithiol, at room temperature and in the absence of any promoter, neatly brings about the S–S → 2SH change, and the latter can be isolated as acrylonitrile adducts; the methodology has been tested with several substrates including c-lysozyme, insulin and oxytocin, and spontaneous imidazole promoted S-deprotection was observed in the case of Z-Cys(S-CH2CH2CN)His-OMe.

  丙烷-1,3-二硫醇在室温下，在没有任何促进剂的情况下，巧妙地引起S→S→2SH变化，后者可以作为丙烯腈加合物分离出来；该方法已使用多种底物（包括 c-溶菌酶、胰岛素和催产素）进行了测试，并且在 Z-Cys(S-CH2CH2CN)His-OMe 的情况下观察到自发咪唑促进的 S-去保护。